Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Ye, Yang; Ma, Guobin; Yao, Kai; Gong, Hegui

doi:10.1055/a-1328-0352

Cited by 7 publications

(1 citation statement)

References 7 publications

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“…Zhang, 15 Engle, 16 and Peng and Qiu 17 continue their studies on Ni-catalyzed difunctionalization of olefins by using fluorinated congeners, heteroleptic complexes or dihalogenated building blocks, accessing molecules that would be beyond reach otherwise. Fu and Wang describe the utilization of N-acylsaccharins in a rather intriguing oxidative transamidation of tertiary aromatic amines, 18 while Gong 19 and Newhouse 20 report the utilization of Ni catalysts in broadly applicable hydrodeoxygenation of alkyl oxalates and benzylic dehydrogenation events.…”

Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Modern Nickel-Catalyzed Reactions

Martı́n

Molander

2021

Synlett

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Ruben Martin is a professor at the Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain. He received his Ph.D. in 2003 from the University of Barcelona under the guidance of Prof. Antoni Riera. In 2004, he moved to the Max-Planck Institut für Kohlenforschung as a Humboldt postdoctoral fellow with Prof. Alois Fürstner. In 2005, he undertook further postdoctoral studies at MIT with Prof. Stephen L. Buchwald as a MEC-Fulbright fellow. In 2008, he began his independent career as an assistant professor at the ICIQ (Tarragona). In 2013, he was promoted to associate professor and shortly after to ICREA Research Professor. Ruben Martin has focused his career on designing synthetically useful Ni-catalyzed methodologies for streamlining the preparation of added-value chemicals from simple precursors without losing sight of mechanistic considerations, when appropriate. Gary A. Molander is a professor at the University of Pennsylvania, Philadelphia, United States. He completed his undergraduate studies in chemistry at Iowa State University under the tutelage of Prof. Richard C. Larock. He earned his Ph.D. at Purdue University under the direction of Prof. Herbert Brown and undertook postdoctoral training with Prof. Barry Trost at the University of Wisconsin, Madison. He began his academic career at the University of Colorado, Boulder, moving to the University of Pennsylvania in 1999, where he is currently Professor of Chemistry. His research interests have focused on the utilization of organolanthanides, Pd-catalyzed cross-coupling reactions with trifluoroborate salts, and the merger of photoredox catalysis and Ni catalysis for tackling a priori uphill transformations under visible-light irradiation for accessing valuable scaffolds in both academic and pharmaceutical laboratories.

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Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Modern Nickel-Catalyzed Reactions

Martı́n

Molander

2021

Synlett

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Ti-Catalyzed Dehydroxylation of Tertiary Alcohols

2022

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Herein we report a Ti-catalyzed direct dehydroxylation of tertiary aliphatic alcohols under mild reaction conditions, forging Barton-type deoxygenation products. This protocol tolerates a wide range of functional groups, including primary alkyl chloride and carbonyl groups. It allows for selective dehydroxylation of tertiary alcohols in diols and the formation of deuterated products with moderate deuterium incorporation. The efficient modification of several drugs and natural products (or their derivatives) highlights the synthetic utility of this method.

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Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides

et al. 2022

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Detailed herein are our synthetic studies toward the preparation of the C18- and C19-benzenoid cephalotane-type norditerpenoids. Guided by chemical network analysis, the core structure of this natural product family was constructed in a concise manner using an iterative cross-coupling, followed by a formal inverse-electron-demand [4 + 2] cycloaddition. Initial efforts to functionalize an alkene group in the [4 + 2] cycloadduct using a Mukaiyama hydration and a subsequent olefination led to the complete C18-carbon framework. While effective, this approach proved lengthy and prompted the development of a direct alkene difunctionalization that relies on borocupration to advance the cycloadduct to the natural products. Late-stage peripheral C–H functionalization facilitated access to all of the known cephanolides in 6–10 steps as well as five recently isolated ceforalides in 8–13 steps.

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Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Cited by 7 publications

References 7 publications

Cluster Preface: Modern Nickel-Catalyzed Reactions

Cluster Preface: Modern Nickel-Catalyzed Reactions

Ti-Catalyzed Dehydroxylation of Tertiary Alcohols

Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides

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